Tetrahydrofuran → HCID 131722554, compound

HRID 1977090Notes

Reaction equation

[CH:1]1[CH:2]=[CH:3][C:4]2[S:9][N:8]=[C:7]([N:10]3[CH2:15][CH2:14][N:13]([CH2:16][CH2:17][C:18]4[CH:19]=[C:20]5[CH2:28][C:26](=[O:27])[NH:25][C:21]5=[CH:22][C:23]=4[Cl:24])[CH2:12][CH2:11]3)[C:5]=2[CH:6]=1.C1COCC1.[CH2:34]([S:36]([OH:39])(=[O:38])=[O:37])[CH3:35]>O>[CH:1]1[CH:2]=[CH:3][C:4]2[S:9][N:8]=[C:7]([N:10]3[CH2:11][CH2:12][N:13]([CH2:16][CH2:17][C:18]4[CH:19]=[C:20]5[CH2:28][C:26](=[O:27])[NH:25][C:21]5=[CH:22][C:23]=4[Cl:24])[CH2:14][CH2:15]3)[C:5]=2[CH:6]=1.[S:36]([CH2:34][CH3:35])([O-:39])(=[O:38])=[O:37]

Participants

Conditions

Temperature: 60 °C

Procedure

1 g of ziprasidone free base was added to 45 mL of THF and 1 mL of water, and the mixture was heated to 60° C. while stirring. The mixture was maintained at 60° C. for two hours, at which time all of the free base had dissolved. 156 mg of ethanesulfonic acid was added and stirring was maintained at 60° C. for two more hours. The mixture turned from light orange to hazy during this time, at which point heating was stopped and the salt started to precipitate. The mixture was allowed to cool to room temperature overnight while stirring continued. The salt was then harvested by filtration as in Example 5.

Workup

temperatureThe mixture was maintained at 60° C. for two hours, at which time all of the free base
dissolutionhad dissolved
stirringstirring
temperaturewas maintained at 60° C. for two more hours
temperatureat which point heating
customto precipitate
temperatureto cool to room temperature overnight
stirringwhile stirring
filtrationThe salt was then harvested by filtration as in Example 5

Sources & evidence

ORD record: ord-5032cbc830b445a99470d3cec41f10fd
Source dataset: uspto-grants-2001_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06232304B1

Reaction notes

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